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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 18:58:23 UTC

Update Date

2022-03-07 02:54:01 UTC

HMDB ID

HMDB0034180

Secondary Accession Numbers

HMDB34180

Metabolite Identification

Common Name

Protohypericin

Description

Protohypericin belongs to the class of organic compounds known as perylenequinones. These are heterocyclic compounds characterized by two 8-hydroxy-1,4-dihydronaphthalen-1-one moieties joined together one or two CC-bonds. Protohypericin has been detected, but not quantified in, several different foods, such as herbs and spices, red tea, black tea, alcoholic beverages, and green tea. This could make protohypericin a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on Protohypericin.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI


  Mrv0541 05061307382D          

 38 44  0  0  0  0            999 V2000
    6.4641    1.9716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9240    2.5952    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3839    1.0361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8439    1.6598    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7342    0.5684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5738    3.0630    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4936   -2.2380    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3333    0.2566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1941    1.1921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1139    2.4393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1139    0.2566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0337    1.5039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4641   -0.2111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7637    2.9071    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9535   -1.6143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8734   -0.3671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3038   -2.0821    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6033    1.0361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6540   -0.3671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4936    2.1275    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3038    0.1007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7637    0.7243    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2236   -0.8348    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6835   -0.2111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5738   -1.3025    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4135    1.1921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0337   -0.6789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9535    0.5684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3839   -1.1466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6835    1.9716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0042   -0.8348    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2236    3.5307    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.7702    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6033   -1.1466    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8439   -2.7057    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0632    1.6598    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9240   -1.7702    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.5952    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  9  1  1  0  0  0  0
  9  3  2  0  0  0  0
  9  5  1  0  0  0  0
 10  2  1  0  0  0  0
 10  4  2  0  0  0  0
 10  6  1  0  0  0  0
 11  3  1  0  0  0  0
 12  4  1  0  0  0  0
 13  5  2  0  0  0  0
 14  6  2  0  0  0  0
 15  7  2  0  0  0  0
 16  8  2  0  0  0  0
 17  7  1  0  0  0  0
 18  8  1  0  0  0  0
 19 11  2  0  0  0  0
 19 13  1  0  0  0  0
 20 12  2  0  0  0  0
 20 14  1  0  0  0  0
 21 11  1  0  0  0  0
 22 12  1  0  0  0  0
 22 21  1  0  0  0  0
 23 15  1  0  0  0  0
 24 16  1  0  0  0  0
 24 23  2  0  0  0  0
 25 17  2  0  0  0  0
 26 18  2  0  0  0  0
 27 21  2  0  0  0  0
 27 23  1  0  0  0  0
 27 25  1  0  0  0  0
 28 22  2  0  0  0  0
 28 24  1  0  0  0  0
 28 26  1  0  0  0  0
 29 19  1  0  0  0  0
 29 25  1  0  0  0  0
 30 20  1  0  0  0  0
 30 26  1  0  0  0  0
 31 13  1  0  0  0  0
 32 14  1  0  0  0  0
 33 15  1  0  0  0  0
 34 16  1  0  0  0  0
 35 17  1  0  0  0  0
 36 18  1  0  0  0  0
 37 29  2  0  0  0  0
 38 30  2  0  0  0  0
M  END

HMDB0034180
     RDKit          3D
Protohypericin
 56 62  0  0  0  0  0  0  0  0999 V2000
   -2.5312    3.9329   -0.0427 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9385    2.8872   -0.9441 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2083    2.9605   -2.2901 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6849    2.0104   -3.1431 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9460    2.0580   -4.5031 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8986    1.0290   -2.5584 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8273   -0.1273   -3.3833 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1074   -0.0812   -4.5989 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4422   -1.3184   -2.8330 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5261   -2.4643   -3.6224 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8674   -2.2945   -4.9533 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2754   -3.6742   -3.0642 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0650   -3.8107   -1.7211 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2696   -5.0753   -1.3323 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1554   -2.6901   -0.9412 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4107   -2.7943    0.4160 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7476   -3.9883    0.9635 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7916   -5.1718    0.3266 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0906   -4.0355    2.3162 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1053   -2.9321    3.1125 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4311   -2.9715    4.4075 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7580   -1.6945    2.5397 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9151   -0.5801    3.3133 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2132   -0.6913    4.5151 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7294    0.6878    2.7106 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3084    1.7065    3.4536 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5903    1.5372    4.8168 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6046    2.8972    2.8277 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3138    3.0084    1.4859 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6789    4.3195    0.8618 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7350    1.9949    0.7837 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3783    0.7505    1.3881 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1804   -0.3736    0.6266 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4189   -1.6370    1.2392 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1315   -0.2727   -0.6884 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5674    0.9009   -1.2359 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1564    1.9028   -0.4127 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1012   -1.4280   -1.5296 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6252    3.7269   -0.0099 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3675    4.9242   -0.5004 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0816    3.8865    0.9657 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8187    3.7503   -2.6771 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5112    2.7586   -4.9374 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9524   -3.0972   -5.5907 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3556   -4.5384   -3.7303 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1839   -5.8917   -1.9542 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0644   -6.0570    0.7805 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3653   -4.9916    2.7905 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6018   -2.7718    5.2481 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0054    2.2643    5.3701 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0463    3.6887    3.4016 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7115    4.5968    1.1309 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5396    4.2088   -0.2279 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9463    5.0575    1.2523 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7917    2.1602   -0.2905 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2253    1.8481    0.6721 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  4  6  2  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 10 12  2  0
 12 13  1  0
 13 14  1  0
 13 15  2  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 17 19  2  0
 19 20  1  0
 20 21  1  0
 20 22  2  0
 22 23  1  0
 23 24  2  0
 23 25  1  0
 25 26  2  0
 26 27  1  0
 26 28  1  0
 28 29  2  0
 29 30  1  0
 29 31  1  0
 31 32  2  0
 32 33  1  0
 33 34  1  0
 33 35  2  0
 35 36  1  0
 36 37  2  0
 35 38  1  0
 37  2  1  0
 36  6  1  0
 38  9  2  0
 38 15  1  0
 34 16  2  0
 34 22  1  0
 32 25  1  0
  1 39  1  0
  1 40  1  0
  1 41  1  0
  3 42  1  0
  5 43  1  0
 11 44  1  0
 12 45  1  0
 14 46  1  0
 18 47  1  0
 19 48  1  0
 21 49  1  0
 27 50  1  0
 28 51  1  0
 30 52  1  0
 30 53  1  0
 30 54  1  0
 31 55  1  0
 37 56  1  0
M  END


  Mrv0541 05061307382D          

 38 44  0  0  0  0            999 V2000
    6.4641    1.9716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9240    2.5952    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3839    1.0361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8439    1.6598    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7342    0.5684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5738    3.0630    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4936   -2.2380    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3333    0.2566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1941    1.1921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1139    2.4393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1139    0.2566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0337    1.5039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4641   -0.2111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7637    2.9071    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9535   -1.6143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8734   -0.3671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3038   -2.0821    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6033    1.0361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6540   -0.3671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4936    2.1275    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3038    0.1007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7637    0.7243    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2236   -0.8348    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6835   -0.2111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5738   -1.3025    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4135    1.1921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0337   -0.6789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9535    0.5684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3839   -1.1466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6835    1.9716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0042   -0.8348    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2236    3.5307    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.7702    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6033   -1.1466    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8439   -2.7057    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0632    1.6598    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9240   -1.7702    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.5952    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  9  1  1  0  0  0  0
  9  3  2  0  0  0  0
  9  5  1  0  0  0  0
 10  2  1  0  0  0  0
 10  4  2  0  0  0  0
 10  6  1  0  0  0  0
 11  3  1  0  0  0  0
 12  4  1  0  0  0  0
 13  5  2  0  0  0  0
 14  6  2  0  0  0  0
 15  7  2  0  0  0  0
 16  8  2  0  0  0  0
 17  7  1  0  0  0  0
 18  8  1  0  0  0  0
 19 11  2  0  0  0  0
 19 13  1  0  0  0  0
 20 12  2  0  0  0  0
 20 14  1  0  0  0  0
 21 11  1  0  0  0  0
 22 12  1  0  0  0  0
 22 21  1  0  0  0  0
 23 15  1  0  0  0  0
 24 16  1  0  0  0  0
 24 23  2  0  0  0  0
 25 17  2  0  0  0  0
 26 18  2  0  0  0  0
 27 21  2  0  0  0  0
 27 23  1  0  0  0  0
 27 25  1  0  0  0  0
 28 22  2  0  0  0  0
 28 24  1  0  0  0  0
 28 26  1  0  0  0  0
 29 19  1  0  0  0  0
 29 25  1  0  0  0  0
 30 20  1  0  0  0  0
 30 26  1  0  0  0  0
 31 13  1  0  0  0  0
 32 14  1  0  0  0  0
 33 15  1  0  0  0  0
 34 16  1  0  0  0  0
 35 17  1  0  0  0  0
 36 18  1  0  0  0  0
 37 29  2  0  0  0  0
 38 30  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0034180

> <DATABASE_NAME>
hmdb

> <SMILES>
CC1=CC2=C(C(O)=C1)C(=O)C1=C(O)C=C(O)C3=C4C(O)=CC(O)=C5C(=O)C6=C(C=C(C)C=C6O)C(C2=C13)=C45

> <INCHI_IDENTIFIER>
InChI=1S/C30H18O8/c1-9-3-11-19(13(31)5-9)29(37)25-17(35)7-15(33)23-24-16(34)8-18(36)26-28(24)22(21(11)27(23)25)12-4-10(2)6-14(32)20(12)30(26)38/h3-8,31-36H,1-2H3

> <INCHI_KEY>
YLILOANQCQKPOD-UHFFFAOYSA-N

> <FORMULA>
C30H18O8

> <MOLECULAR_WEIGHT>
506.4591

> <EXACT_MASS>
506.100167552

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_AVERAGE_POLARIZABILITY>
51.1511340881561

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
7,11,13,16,18,22-hexahydroxy-5,24-dimethylheptacyclo[13.11.1.1²,¹⁰.0³,⁸.0¹⁹,²⁷.0²¹,²⁶.0¹⁴,²⁸]octacosa-1(27),2(28),3(8),4,6,10,12,14,16,18,21(26),22,24-tridecaene-9,20-dione

> <ALOGPS_LOGP>
3.99

> <JCHEM_LOGP>
8.024315344666666

> <ALOGPS_LOGS>
-5.01

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-4

> <JCHEM_PKA>
4.471227883026972

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.5294788338363703

> <JCHEM_PKA_STRONGEST_BASIC>
11.29126967391554

> <JCHEM_POLAR_SURFACE_AREA>
155.52

> <JCHEM_REFRACTIVITY>
140.2336

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
5.00e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
7,11,13,16,18,22-hexahydroxy-5,24-dimethylheptacyclo[13.11.1.1²,¹⁰.0³,⁸.0¹⁹,²⁷.0²¹,²⁶.0¹⁴,²⁸]octacosa-1(27),2(28),3(8),4,6,10,12,14,16,18,21(26),22,24-tridecaene-9,20-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0034180
     RDKit          3D
Protohypericin
 56 62  0  0  0  0  0  0  0  0999 V2000
   -2.5312    3.9329   -0.0427 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9385    2.8872   -0.9441 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2083    2.9605   -2.2901 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6849    2.0104   -3.1431 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9460    2.0580   -4.5031 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8986    1.0290   -2.5584 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8273   -0.1273   -3.3833 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1074   -0.0812   -4.5989 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4422   -1.3184   -2.8330 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5261   -2.4643   -3.6224 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8674   -2.2945   -4.9533 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2754   -3.6742   -3.0642 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0650   -3.8107   -1.7211 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2696   -5.0753   -1.3323 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1554   -2.6901   -0.9412 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4107   -2.7943    0.4160 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7476   -3.9883    0.9635 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7916   -5.1718    0.3266 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0906   -4.0355    2.3162 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1053   -2.9321    3.1125 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4311   -2.9715    4.4075 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7580   -1.6945    2.5397 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9151   -0.5801    3.3133 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2132   -0.6913    4.5151 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7294    0.6878    2.7106 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3084    1.7065    3.4536 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5903    1.5372    4.8168 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6046    2.8972    2.8277 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3138    3.0084    1.4859 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6789    4.3195    0.8618 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7350    1.9949    0.7837 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3783    0.7505    1.3881 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1804   -0.3736    0.6266 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4189   -1.6370    1.2392 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1315   -0.2727   -0.6884 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5674    0.9009   -1.2359 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1564    1.9028   -0.4127 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1012   -1.4280   -1.5296 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6252    3.7269   -0.0099 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3675    4.9242   -0.5004 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0816    3.8865    0.9657 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8187    3.7503   -2.6771 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5112    2.7586   -4.9374 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9524   -3.0972   -5.5907 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3556   -4.5384   -3.7303 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1839   -5.8917   -1.9542 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0644   -6.0570    0.7805 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3653   -4.9916    2.7905 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6018   -2.7718    5.2481 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0054    2.2643    5.3701 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0463    3.6887    3.4016 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7115    4.5968    1.1309 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5396    4.2088   -0.2279 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9463    5.0575    1.2523 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7917    2.1602   -0.2905 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2253    1.8481    0.6721 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  4  6  2  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 10 12  2  0
 12 13  1  0
 13 14  1  0
 13 15  2  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 17 19  2  0
 19 20  1  0
 20 21  1  0
 20 22  2  0
 22 23  1  0
 23 24  2  0
 23 25  1  0
 25 26  2  0
 26 27  1  0
 26 28  1  0
 28 29  2  0
 29 30  1  0
 29 31  1  0
 31 32  2  0
 32 33  1  0
 33 34  1  0
 33 35  2  0
 35 36  1  0
 36 37  2  0
 35 38  1  0
 37  2  1  0
 36  6  1  0
 38  9  2  0
 38 15  1  0
 34 16  2  0
 34 22  1  0
 32 25  1  0
  1 39  1  0
  1 40  1  0
  1 41  1  0
  3 42  1  0
  5 43  1  0
 11 44  1  0
 12 45  1  0
 14 46  1  0
 18 47  1  0
 19 48  1  0
 21 49  1  0
 27 50  1  0
 28 51  1  0
 30 52  1  0
 30 53  1  0
 30 54  1  0
 31 55  1  0
 37 56  1  0
M  END

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0      12.066   3.680   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      11.058   4.844   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      10.050   1.934   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       9.042   3.098   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      12.571   1.061   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.538   5.718   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.521  -4.178   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.489   0.479   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      11.562   2.225   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       9.546   4.553   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       9.546   0.479   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       7.530   2.807   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      12.066  -0.394   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       7.026   5.427   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.513  -3.013   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.497  -0.685   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       8.034  -3.887   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.993   1.934   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      10.554  -0.685   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       6.521   3.971   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       8.034   0.188   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       7.026   1.352   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       6.017  -1.558   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       5.009  -0.394   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       8.538  -2.431   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       4.505   2.225   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       7.530  -1.267   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       5.513   1.061   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      10.050  -2.140   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       5.009   3.680   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      13.075  -1.558   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0       6.017   6.591   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0       4.001  -3.304   0.000  0.00  0.00           O+0
HETATM   34  O   UNK     0       2.993  -2.140   0.000  0.00  0.00           O+0
HETATM   35  O   UNK     0       9.042  -5.051   0.000  0.00  0.00           O+0
HETATM   36  O   UNK     0       1.985   3.098   0.000  0.00  0.00           O+0
HETATM   37  O   UNK     0      11.058  -3.304   0.000  0.00  0.00           O+0
HETATM   38  O   UNK     0       4.001   4.844   0.000  0.00  0.00           O+0
CONECT    1    9                                                            
CONECT    2   10                                                            
CONECT    3    9   11                                                       
CONECT    4   10   12                                                       
CONECT    5    9   13                                                       
CONECT    6   10   14                                                       
CONECT    7   15   17                                                       
CONECT    8   16   18                                                       
CONECT    9    1    3    5                                                  
CONECT   10    2    4    6                                                  
CONECT   11    3   19   21                                                  
CONECT   12    4   20   22                                                  
CONECT   13    5   19   31                                                  
CONECT   14    6   20   32                                                  
CONECT   15    7   23   33                                                  
CONECT   16    8   24   34                                                  
CONECT   17    7   25   35                                                  
CONECT   18    8   26   36                                                  
CONECT   19   11   13   29                                                  
CONECT   20   12   14   30                                                  
CONECT   21   11   22   27                                                  
CONECT   22   12   21   28                                                  
CONECT   23   15   24   27                                                  
CONECT   24   16   23   28                                                  
CONECT   25   17   27   29                                                  
CONECT   26   18   28   30                                                  
CONECT   27   21   23   25                                                  
CONECT   28   22   24   26                                                  
CONECT   29   19   25   37                                                  
CONECT   30   20   26   38                                                  
CONECT   31   13                                                            
CONECT   32   14                                                            
CONECT   33   15                                                            
CONECT   34   16                                                            
CONECT   35   17                                                            
CONECT   36   18                                                            
CONECT   37   29                                                            
CONECT   38   30                                                            
MASTER        0    0    0    0    0    0    0    0   38    0   88    0
END

COMPND    HMDB0034180
HETATM    1  C1  UNL     1      -2.531   3.933  -0.043  1.00  0.00           C  
HETATM    2  C2  UNL     1      -1.938   2.887  -0.944  1.00  0.00           C  
HETATM    3  C3  UNL     1      -2.208   2.960  -2.290  1.00  0.00           C  
HETATM    4  C4  UNL     1      -1.685   2.010  -3.143  1.00  0.00           C  
HETATM    5  O1  UNL     1      -1.946   2.058  -4.503  1.00  0.00           O  
HETATM    6  C5  UNL     1      -0.899   1.029  -2.558  1.00  0.00           C  
HETATM    7  C6  UNL     1      -0.827  -0.127  -3.383  1.00  0.00           C  
HETATM    8  O2  UNL     1      -1.107  -0.081  -4.599  1.00  0.00           O  
HETATM    9  C7  UNL     1      -0.442  -1.318  -2.833  1.00  0.00           C  
HETATM   10  C8  UNL     1      -0.526  -2.464  -3.622  1.00  0.00           C  
HETATM   11  O3  UNL     1      -0.867  -2.295  -4.953  1.00  0.00           O  
HETATM   12  C9  UNL     1      -0.275  -3.674  -3.064  1.00  0.00           C  
HETATM   13  C10 UNL     1       0.065  -3.811  -1.721  1.00  0.00           C  
HETATM   14  O4  UNL     1       0.270  -5.075  -1.332  1.00  0.00           O  
HETATM   15  C11 UNL     1       0.155  -2.690  -0.941  1.00  0.00           C  
HETATM   16  C12 UNL     1       0.411  -2.794   0.416  1.00  0.00           C  
HETATM   17  C13 UNL     1       0.748  -3.988   0.963  1.00  0.00           C  
HETATM   18  O5  UNL     1       0.792  -5.172   0.327  1.00  0.00           O  
HETATM   19  C14 UNL     1       1.091  -4.036   2.316  1.00  0.00           C  
HETATM   20  C15 UNL     1       1.105  -2.932   3.112  1.00  0.00           C  
HETATM   21  O6  UNL     1       1.431  -2.971   4.407  1.00  0.00           O  
HETATM   22  C16 UNL     1       0.758  -1.694   2.540  1.00  0.00           C  
HETATM   23  C17 UNL     1       0.915  -0.580   3.313  1.00  0.00           C  
HETATM   24  O7  UNL     1       1.213  -0.691   4.515  1.00  0.00           O  
HETATM   25  C18 UNL     1       0.729   0.688   2.711  1.00  0.00           C  
HETATM   26  C19 UNL     1       1.308   1.707   3.454  1.00  0.00           C  
HETATM   27  O8  UNL     1       1.590   1.537   4.817  1.00  0.00           O  
HETATM   28  C20 UNL     1       1.605   2.897   2.828  1.00  0.00           C  
HETATM   29  C21 UNL     1       1.314   3.008   1.486  1.00  0.00           C  
HETATM   30  C22 UNL     1       1.679   4.320   0.862  1.00  0.00           C  
HETATM   31  C23 UNL     1       0.735   1.995   0.784  1.00  0.00           C  
HETATM   32  C24 UNL     1       0.378   0.750   1.388  1.00  0.00           C  
HETATM   33  C25 UNL     1       0.180  -0.374   0.627  1.00  0.00           C  
HETATM   34  C26 UNL     1       0.419  -1.637   1.239  1.00  0.00           C  
HETATM   35  C27 UNL     1      -0.131  -0.273  -0.688  1.00  0.00           C  
HETATM   36  C28 UNL     1      -0.567   0.901  -1.236  1.00  0.00           C  
HETATM   37  C29 UNL     1      -1.156   1.903  -0.413  1.00  0.00           C  
HETATM   38  C30 UNL     1      -0.101  -1.428  -1.530  1.00  0.00           C  
HETATM   39  H1  UNL     1      -3.625   3.727  -0.010  1.00  0.00           H  
HETATM   40  H2  UNL     1      -2.368   4.924  -0.500  1.00  0.00           H  
HETATM   41  H3  UNL     1      -2.082   3.886   0.966  1.00  0.00           H  
HETATM   42  H4  UNL     1      -2.819   3.750  -2.677  1.00  0.00           H  
HETATM   43  H5  UNL     1      -2.511   2.759  -4.937  1.00  0.00           H  
HETATM   44  H6  UNL     1      -0.952  -3.097  -5.591  1.00  0.00           H  
HETATM   45  H7  UNL     1      -0.356  -4.538  -3.730  1.00  0.00           H  
HETATM   46  H8  UNL     1       0.184  -5.892  -1.954  1.00  0.00           H  
HETATM   47  H9  UNL     1       1.064  -6.057   0.781  1.00  0.00           H  
HETATM   48  H10 UNL     1       1.365  -4.992   2.791  1.00  0.00           H  
HETATM   49  H11 UNL     1       1.602  -2.772   5.248  1.00  0.00           H  
HETATM   50  H12 UNL     1       2.005   2.264   5.370  1.00  0.00           H  
HETATM   51  H13 UNL     1       2.046   3.689   3.402  1.00  0.00           H  
HETATM   52  H14 UNL     1       2.712   4.597   1.131  1.00  0.00           H  
HETATM   53  H15 UNL     1       1.540   4.209  -0.228  1.00  0.00           H  
HETATM   54  H16 UNL     1       0.946   5.058   1.252  1.00  0.00           H  
HETATM   55  H17 UNL     1       0.792   2.160  -0.290  1.00  0.00           H  
HETATM   56  H18 UNL     1      -1.225   1.848   0.672  1.00  0.00           H  
CONECT    1    2   39   40   41
CONECT    2    3    3   37
CONECT    3    4   42
CONECT    4    5    6    6
CONECT    5   43
CONECT    6    7   36
CONECT    7    8    8    9
CONECT    9   10   38   38
CONECT   10   11   12   12
CONECT   11   44
CONECT   12   13   45
CONECT   13   14   15   15
CONECT   14   46
CONECT   15   16   38
CONECT   16   17   34   34
CONECT   17   18   19   19
CONECT   18   47
CONECT   19   20   48
CONECT   20   21   22   22
CONECT   21   49
CONECT   22   23   34
CONECT   23   24   24   25
CONECT   25   26   26   32
CONECT   26   27   28
CONECT   27   50
CONECT   28   29   29   51
CONECT   29   30   31
CONECT   30   52   53   54
CONECT   31   32   32   55
CONECT   32   33
CONECT   33   34   35   35
CONECT   35   36   38
CONECT   36   37   37
CONECT   37   56
END

HMDB0034180
     RDKit          3D
Protohypericin
 56 62  0  0  0  0  0  0  0  0999 V2000
   -2.5312    3.9329   -0.0427 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9385    2.8872   -0.9441 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2083    2.9605   -2.2901 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6849    2.0104   -3.1431 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9460    2.0580   -4.5031 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8986    1.0290   -2.5584 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8273   -0.1273   -3.3833 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1074   -0.0812   -4.5989 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4422   -1.3184   -2.8330 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5261   -2.4643   -3.6224 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8674   -2.2945   -4.9533 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2754   -3.6742   -3.0642 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0650   -3.8107   -1.7211 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2696   -5.0753   -1.3323 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1554   -2.6901   -0.9412 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4107   -2.7943    0.4160 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7476   -3.9883    0.9635 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7916   -5.1718    0.3266 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0906   -4.0355    2.3162 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1053   -2.9321    3.1125 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4311   -2.9715    4.4075 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7580   -1.6945    2.5397 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9151   -0.5801    3.3133 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2132   -0.6913    4.5151 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7294    0.6878    2.7106 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3084    1.7065    3.4536 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5903    1.5372    4.8168 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6046    2.8972    2.8277 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3138    3.0084    1.4859 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6789    4.3195    0.8618 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7350    1.9949    0.7837 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3783    0.7505    1.3881 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1804   -0.3736    0.6266 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4189   -1.6370    1.2392 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1315   -0.2727   -0.6884 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5674    0.9009   -1.2359 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1564    1.9028   -0.4127 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1012   -1.4280   -1.5296 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6252    3.7269   -0.0099 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3675    4.9242   -0.5004 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0816    3.8865    0.9657 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8187    3.7503   -2.6771 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5112    2.7586   -4.9374 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9524   -3.0972   -5.5907 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3556   -4.5384   -3.7303 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1839   -5.8917   -1.9542 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0644   -6.0570    0.7805 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3653   -4.9916    2.7905 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6018   -2.7718    5.2481 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0054    2.2643    5.3701 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0463    3.6887    3.4016 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7115    4.5968    1.1309 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5396    4.2088   -0.2279 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9463    5.0575    1.2523 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7917    2.1602   -0.2905 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2253    1.8481    0.6721 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  4  6  2  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 10 12  2  0
 12 13  1  0
 13 14  1  0
 13 15  2  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 17 19  2  0
 19 20  1  0
 20 21  1  0
 20 22  2  0
 22 23  1  0
 23 24  2  0
 23 25  1  0
 25 26  2  0
 26 27  1  0
 26 28  1  0
 28 29  2  0
 29 30  1  0
 29 31  1  0
 31 32  2  0
 32 33  1  0
 33 34  1  0
 33 35  2  0
 35 36  1  0
 36 37  2  0
 35 38  1  0
 37  2  1  0
 36  6  1  0
 38  9  2  0
 38 15  1  0
 34 16  2  0
 34 22  1  0
 32 25  1  0
  1 39  1  0
  1 40  1  0
  1 41  1  0
  3 42  1  0
  5 43  1  0
 11 44  1  0
 12 45  1  0
 14 46  1  0
 18 47  1  0
 19 48  1  0
 21 49  1  0
 27 50  1  0
 28 51  1  0
 30 52  1  0
 30 53  1  0
 30 54  1  0
 31 55  1  0
 37 56  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Protohypericin	MeSH

Chemical Formula

C₃₀H₁₈O₈

Average Molecular Weight

506.4591

Monoisotopic Molecular Weight

506.100167552

IUPAC Name

7,11,13,16,18,22-hexahydroxy-5,24-dimethylheptacyclo[13.11.1.1²,¹⁰.0³,⁸.0¹⁹,²⁷.0²¹,²⁶.0¹⁴,²⁸]octacosa-1(27),2(28),3(8),4,6,10,12,14,16,18,21(26),22,24-tridecaene-9,20-dione

Traditional Name

7,11,13,16,18,22-hexahydroxy-5,24-dimethylheptacyclo[13.11.1.1²,¹⁰.0³,⁸.0¹⁹,²⁷.0²¹,²⁶.0¹⁴,²⁸]octacosa-1(27),2(28),3(8),4,6,10,12,14,16,18,21(26),22,24-tridecaene-9,20-dione

CAS Registry Number

548-03-8

SMILES

CC1=CC2=C(C(O)=C1)C(=O)C1=C(O)C=C(O)C3=C4C(O)=CC(O)=C5C(=O)C6=C(C=C(C)C=C6O)C(C2=C13)=C45

InChI Identifier

InChI=1S/C30H18O8/c1-9-3-11-19(13(31)5-9)29(37)25-17(35)7-15(33)23-24-16(34)8-18(36)26-28(24)22(21(11)27(23)25)12-4-10(2)6-14(32)20(12)30(26)38/h3-8,31-36H,1-2H3

InChI Key

YLILOANQCQKPOD-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as perylenequinones. These are heterocyclic compounds characterized by two 8-hydroxy-1,4-dihydronaphthalen-1-one moieties joined together one or two CC-bonds.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Perylenequinones

Sub Class

Not Available

Direct Parent

Perylenequinones

Alternative Parents

Substituents

Perylenequinone
Phenanthrol
Phenanthrene
Anthracene
1-naphthol
2-naphthol
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Vinylogous acid
Polyol
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0034180)
Cell membrane (HMDB: HMDB0034180)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0034180)

Source

Exogenous

Exogenous (HMDB: HMDB0034180)

Food

Food (HMDB: HMDB0034180)

Tea

Herb and spice

Herbs and Spices (FooDB: FOOD00866)

Beverage

Alcoholic beverage

Alcoholic beverages (FooDB: FOOD00854)

Endogenous

Plant

Plant (HMDB: HMDB0034180)

Process

Not Available

Role

Biological role

Nutrient (HMDB: HMDB0034180)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	300 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.005 g/L	ALOGPS
logP	3.99	ALOGPS
logP	8.02	ChemAxon
logS	-5	ALOGPS
pKa (Strongest Acidic)	3.53	ChemAxon
pKa (Strongest Basic)	11.29	ChemAxon
Physiological Charge	-4	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	155.52 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	140.23 m³·mol⁻¹	ChemAxon
Polarizability	51.15 Å³	ChemAxon
Number of Rings	7	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	214.749	31661259
DarkChem	[M-H]-	208.504	31661259
DeepCCS	[M-2H]-	248.82	30932474
DeepCCS	[M+Na]+	223.417	30932474
AllCCS	[M+H]+	214.5	32859911
AllCCS	[M+H-H2O]+	212.5	32859911
AllCCS	[M+NH4]+	216.4	32859911
AllCCS	[M+Na]+	216.9	32859911
AllCCS	[M-H]-	207.2	32859911
AllCCS	[M+Na-2H]-	206.3	32859911
AllCCS	[M+HCOO]-	205.6	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	5.0 minutes	32390414
Predicted by Siyang on May 30, 2022	15.8706 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	2.82 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	3228.4 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	258.8 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	132.5 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	161.4 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	463.1 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	789.1 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	680.9 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	138.6 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	944.9 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	566.0 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	2438.4 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	392.5 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	537.0 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	536.7 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	119.2 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	182.3 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Protohypericin	CC1=CC2=C(C(O)=C1)C(=O)C1=C(O)C=C(O)C3=C4C(O)=CC(O)=C5C(=O)C6=C(C=C(C)C=C6O)C(C2=C13)=C45	7408.2	Standard polar	33892256
Protohypericin	CC1=CC2=C(C(O)=C1)C(=O)C1=C(O)C=C(O)C3=C4C(O)=CC(O)=C5C(=O)C6=C(C=C(C)C=C6O)C(C2=C13)=C45	2864.6	Standard non polar	33892256
Protohypericin	CC1=CC2=C(C(O)=C1)C(=O)C1=C(O)C=C(O)C3=C4C(O)=CC(O)=C5C(=O)C6=C(C=C(C)C=C6O)C(C2=C13)=C45	5325.8	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Protohypericin,1TMS,isomer #1	CC1=CC(O)=C2C(=O)C3=C4C(=C(O)C=C3O)C3=C5C(=C(O)C=C3O)C(=O)C3=C(O[Si](C)(C)C)C=C(C)C=C3C5=C4C2=C1	5331.5	Semi standard non polar	33892256
Protohypericin,1TMS,isomer #2	CC1=CC(O)=C2C(=O)C3=C4C(=C(O)C=C3O)C3=C5C(=C(O[Si](C)(C)C)C=C3O)C(=O)C3=C(O)C=C(C)C=C3C5=C4C2=C1	5342.6	Semi standard non polar	33892256
Protohypericin,1TMS,isomer #3	CC1=CC(O)=C2C(=O)C3=C4C(=C(O)C=C3O)C3=C5C(=C(O)C=C3O[Si](C)(C)C)C(=O)C3=C(O)C=C(C)C=C3C5=C4C2=C1	5350.3	Semi standard non polar	33892256
Protohypericin,2TMS,isomer #1	CC1=CC(O[Si](C)(C)C)=C2C(=O)C3=C4C(=C(O)C=C3O)C3=C5C(=C(O)C=C3O)C(=O)C3=C(O[Si](C)(C)C)C=C(C)C=C3C5=C4C2=C1	5280.8	Semi standard non polar	33892256
Protohypericin,2TMS,isomer #2	CC1=CC(O[Si](C)(C)C)=C2C(=O)C3=C4C(=C(O)C=C3O)C3=C5C(=C(O[Si](C)(C)C)C=C3O)C(=O)C3=C(O)C=C(C)C=C3C5=C4C2=C1	5298.4	Semi standard non polar	33892256
Protohypericin,2TMS,isomer #3	CC1=CC(O[Si](C)(C)C)=C2C(=O)C3=C4C(=C(O)C=C3O)C3=C5C(=C(O)C=C3O[Si](C)(C)C)C(=O)C3=C(O)C=C(C)C=C3C5=C4C2=C1	5306.2	Semi standard non polar	33892256
Protohypericin,2TMS,isomer #4	CC1=CC(O)=C2C(=O)C3=C4C(=C(O)C=C3O)C3=C5C(=C(O)C=C3O[Si](C)(C)C)C(=O)C3=C(O[Si](C)(C)C)C=C(C)C=C3C5=C4C2=C1	5306.7	Semi standard non polar	33892256
Protohypericin,2TMS,isomer #5	CC1=CC(O)=C2C(=O)C3=C4C(=C(O)C=C3O)C3=C5C(=C(O[Si](C)(C)C)C=C3O)C(=O)C3=C(O[Si](C)(C)C)C=C(C)C=C3C5=C4C2=C1	5303.7	Semi standard non polar	33892256
Protohypericin,2TMS,isomer #6	CC1=CC(O)=C2C(=O)C3=C4C(=C(O)C=C3O[Si](C)(C)C)C3=C5C(=C(O[Si](C)(C)C)C=C3O)C(=O)C3=C(O)C=C(C)C=C3C5=C4C2=C1	5316.9	Semi standard non polar	33892256
Protohypericin,2TMS,isomer #7	CC1=CC(O)=C2C(=O)C3=C4C(=C(O)C=C3O[Si](C)(C)C)C3=C5C(=C(O)C=C3O[Si](C)(C)C)C(=O)C3=C(O)C=C(C)C=C3C5=C4C2=C1	5325.0	Semi standard non polar	33892256
Protohypericin,2TMS,isomer #8	CC1=CC(O)=C2C(=O)C3=C4C(=C(O)C=C3O)C3=C5C(=C(O[Si](C)(C)C)C=C3O[Si](C)(C)C)C(=O)C3=C(O)C=C(C)C=C3C5=C4C2=C1	5304.2	Semi standard non polar	33892256
Protohypericin,2TMS,isomer #9	CC1=CC(O)=C2C(=O)C3=C4C(=C(O[Si](C)(C)C)C=C3O)C3=C5C(=C(O)C=C3O[Si](C)(C)C)C(=O)C3=C(O)C=C(C)C=C3C5=C4C2=C1	5344.0	Semi standard non polar	33892256
Protohypericin,3TMS,isomer #1	CC1=CC(O[Si](C)(C)C)=C2C(=O)C3=C4C(=C(O)C=C3O)C3=C5C(=C(O[Si](C)(C)C)C=C3O)C(=O)C3=C(O[Si](C)(C)C)C=C(C)C=C3C5=C4C2=C1	5135.6	Semi standard non polar	33892256
Protohypericin,3TMS,isomer #10	CC1=CC(O)=C2C(=O)C3=C4C(=C(O[Si](C)(C)C)C=C3O)C3=C5C(=C(O[Si](C)(C)C)C=C3O[Si](C)(C)C)C(=O)C3=C(O)C=C(C)C=C3C5=C4C2=C1	5182.9	Semi standard non polar	33892256
Protohypericin,3TMS,isomer #2	CC1=CC(O[Si](C)(C)C)=C2C(=O)C3=C4C(=C(O)C=C3O)C3=C5C(=C(O)C=C3O[Si](C)(C)C)C(=O)C3=C(O[Si](C)(C)C)C=C(C)C=C3C5=C4C2=C1	5144.0	Semi standard non polar	33892256
Protohypericin,3TMS,isomer #3	CC1=CC(O)=C2C(=O)C3=C4C(=C(O)C=C3O[Si](C)(C)C)C3=C5C(=C(O[Si](C)(C)C)C=C3O)C(=O)C3=C(O[Si](C)(C)C)C=C(C)C=C3C5=C4C2=C1	5151.2	Semi standard non polar	33892256
Protohypericin,3TMS,isomer #4	CC1=CC(O)=C2C(=O)C3=C4C(=C(O)C=C3O[Si](C)(C)C)C3=C5C(=C(O)C=C3O[Si](C)(C)C)C(=O)C3=C(O[Si](C)(C)C)C=C(C)C=C3C5=C4C2=C1	5160.3	Semi standard non polar	33892256
Protohypericin,3TMS,isomer #5	CC1=CC(O[Si](C)(C)C)=C2C(=O)C3=C4C(=C(O)C=C3O)C3=C5C(=C(O[Si](C)(C)C)C=C3O[Si](C)(C)C)C(=O)C3=C(O)C=C(C)C=C3C5=C4C2=C1	5152.4	Semi standard non polar	33892256
Protohypericin,3TMS,isomer #6	CC1=CC(O[Si](C)(C)C)=C2C(=O)C3=C4C(=C(O)C=C3O[Si](C)(C)C)C3=C5C(=C(O)C=C3O[Si](C)(C)C)C(=O)C3=C(O)C=C(C)C=C3C5=C4C2=C1	5161.9	Semi standard non polar	33892256
Protohypericin,3TMS,isomer #7	CC1=CC(O)=C2C(=O)C3=C4C(=C(O[Si](C)(C)C)C=C3O)C3=C5C(=C(O)C=C3O[Si](C)(C)C)C(=O)C3=C(O[Si](C)(C)C)C=C(C)C=C3C5=C4C2=C1	5176.6	Semi standard non polar	33892256
Protohypericin,3TMS,isomer #8	CC1=CC(O)=C2C(=O)C3=C4C(=C(O)C=C3O)C3=C5C(=C(O[Si](C)(C)C)C=C3O[Si](C)(C)C)C(=O)C3=C(O[Si](C)(C)C)C=C(C)C=C3C5=C4C2=C1	5154.8	Semi standard non polar	33892256
Protohypericin,3TMS,isomer #9	CC1=CC(O)=C2C(=O)C3=C4C(=C(O)C=C3O[Si](C)(C)C)C3=C5C(=C(O[Si](C)(C)C)C=C3O[Si](C)(C)C)C(=O)C3=C(O)C=C(C)C=C3C5=C4C2=C1	5166.3	Semi standard non polar	33892256
Protohypericin,4TMS,isomer #1	CC1=CC(O[Si](C)(C)C)=C2C(=O)C3=C4C(=C(O)C=C3O[Si](C)(C)C)C3=C5C(=C(O[Si](C)(C)C)C=C3O)C(=O)C3=C(O[Si](C)(C)C)C=C(C)C=C3C5=C4C2=C1	4984.6	Semi standard non polar	33892256
Protohypericin,4TMS,isomer #2	CC1=CC(O[Si](C)(C)C)=C2C(=O)C3=C4C(=C(O)C=C3O[Si](C)(C)C)C3=C5C(=C(O)C=C3O[Si](C)(C)C)C(=O)C3=C(O[Si](C)(C)C)C=C(C)C=C3C5=C4C2=C1	4985.4	Semi standard non polar	33892256
Protohypericin,4TMS,isomer #3	CC1=CC(O[Si](C)(C)C)=C2C(=O)C3=C4C(=C(O)C=C3O)C3=C5C(=C(O[Si](C)(C)C)C=C3O[Si](C)(C)C)C(=O)C3=C(O[Si](C)(C)C)C=C(C)C=C3C5=C4C2=C1	4986.1	Semi standard non polar	33892256
Protohypericin,4TMS,isomer #4	CC1=CC(O[Si](C)(C)C)=C2C(=O)C3=C4C(=C(O[Si](C)(C)C)C=C3O)C3=C5C(=C(O)C=C3O[Si](C)(C)C)C(=O)C3=C(O[Si](C)(C)C)C=C(C)C=C3C5=C4C2=C1	4995.0	Semi standard non polar	33892256
Protohypericin,4TMS,isomer #5	CC1=CC(O[Si](C)(C)C)=C2C(=O)C3=C4C(=C(O)C=C3O[Si](C)(C)C)C3=C5C(=C(O[Si](C)(C)C)C=C3O[Si](C)(C)C)C(=O)C3=C(O)C=C(C)C=C3C5=C4C2=C1	4991.0	Semi standard non polar	33892256
Protohypericin,4TMS,isomer #6	CC1=CC(O)=C2C(=O)C3=C4C(=C(O)C=C3O[Si](C)(C)C)C3=C5C(=C(O[Si](C)(C)C)C=C3O[Si](C)(C)C)C(=O)C3=C(O[Si](C)(C)C)C=C(C)C=C3C5=C4C2=C1	4992.1	Semi standard non polar	33892256
Protohypericin,4TMS,isomer #7	CC1=CC(O[Si](C)(C)C)=C2C(=O)C3=C4C(=C(O[Si](C)(C)C)C=C3O)C3=C5C(=C(O[Si](C)(C)C)C=C3O[Si](C)(C)C)C(=O)C3=C(O)C=C(C)C=C3C5=C4C2=C1	5000.6	Semi standard non polar	33892256
Protohypericin,4TMS,isomer #8	CC1=CC(O)=C2C(=O)C3=C4C(=C(O[Si](C)(C)C)C=C3O)C3=C5C(=C(O[Si](C)(C)C)C=C3O[Si](C)(C)C)C(=O)C3=C(O[Si](C)(C)C)C=C(C)C=C3C5=C4C2=C1	5007.2	Semi standard non polar	33892256
Protohypericin,4TMS,isomer #9	CC1=CC(O)=C2C(=O)C3=C4C(=C(O[Si](C)(C)C)C=C3O[Si](C)(C)C)C3=C5C(=C(O[Si](C)(C)C)C=C3O[Si](C)(C)C)C(=O)C3=C(O)C=C(C)C=C3C5=C4C2=C1	5003.3	Semi standard non polar	33892256
Protohypericin,5TMS,isomer #1	CC1=CC(O[Si](C)(C)C)=C2C(=O)C3=C4C(=C(O)C=C3O[Si](C)(C)C)C3=C5C(=C(O[Si](C)(C)C)C=C3O[Si](C)(C)C)C(=O)C3=C(O[Si](C)(C)C)C=C(C)C=C3C5=C4C2=C1	4828.9	Semi standard non polar	33892256
Protohypericin,5TMS,isomer #2	CC1=CC(O[Si](C)(C)C)=C2C(=O)C3=C4C(=C(O[Si](C)(C)C)C=C3O)C3=C5C(=C(O[Si](C)(C)C)C=C3O[Si](C)(C)C)C(=O)C3=C(O[Si](C)(C)C)C=C(C)C=C3C5=C4C2=C1	4832.0	Semi standard non polar	33892256
Protohypericin,5TMS,isomer #3	CC1=CC(O)=C2C(=O)C3=C4C(=C(O[Si](C)(C)C)C=C3O[Si](C)(C)C)C3=C5C(=C(O[Si](C)(C)C)C=C3O[Si](C)(C)C)C(=O)C3=C(O[Si](C)(C)C)C=C(C)C=C3C5=C4C2=C1	4842.0	Semi standard non polar	33892256
Protohypericin,1TBDMS,isomer #1	CC1=CC(O)=C2C(=O)C3=C4C(=C(O)C=C3O)C3=C5C(=C(O)C=C3O)C(=O)C3=C(O[Si](C)(C)C(C)(C)C)C=C(C)C=C3C5=C4C2=C1	5534.7	Semi standard non polar	33892256
Protohypericin,1TBDMS,isomer #2	CC1=CC(O)=C2C(=O)C3=C4C(=C(O)C=C3O)C3=C5C(=C(O[Si](C)(C)C(C)(C)C)C=C3O)C(=O)C3=C(O)C=C(C)C=C3C5=C4C2=C1	5546.7	Semi standard non polar	33892256
Protohypericin,1TBDMS,isomer #3	CC1=CC(O)=C2C(=O)C3=C4C(=C(O)C=C3O)C3=C5C(=C(O)C=C3O[Si](C)(C)C(C)(C)C)C(=O)C3=C(O)C=C(C)C=C3C5=C4C2=C1	5551.0	Semi standard non polar	33892256
Protohypericin,2TBDMS,isomer #1	CC1=CC(O[Si](C)(C)C(C)(C)C)=C2C(=O)C3=C4C(=C(O)C=C3O)C3=C5C(=C(O)C=C3O)C(=O)C3=C(O[Si](C)(C)C(C)(C)C)C=C(C)C=C3C5=C4C2=C1	5671.8	Semi standard non polar	33892256
Protohypericin,2TBDMS,isomer #2	CC1=CC(O[Si](C)(C)C(C)(C)C)=C2C(=O)C3=C4C(=C(O)C=C3O)C3=C5C(=C(O[Si](C)(C)C(C)(C)C)C=C3O)C(=O)C3=C(O)C=C(C)C=C3C5=C4C2=C1	5696.3	Semi standard non polar	33892256
Protohypericin,2TBDMS,isomer #3	CC1=CC(O[Si](C)(C)C(C)(C)C)=C2C(=O)C3=C4C(=C(O)C=C3O)C3=C5C(=C(O)C=C3O[Si](C)(C)C(C)(C)C)C(=O)C3=C(O)C=C(C)C=C3C5=C4C2=C1	5701.5	Semi standard non polar	33892256
Protohypericin,2TBDMS,isomer #4	CC1=CC(O)=C2C(=O)C3=C4C(=C(O)C=C3O)C3=C5C(=C(O)C=C3O[Si](C)(C)C(C)(C)C)C(=O)C3=C(O[Si](C)(C)C(C)(C)C)C=C(C)C=C3C5=C4C2=C1	5700.4	Semi standard non polar	33892256
Protohypericin,2TBDMS,isomer #5	CC1=CC(O)=C2C(=O)C3=C4C(=C(O)C=C3O)C3=C5C(=C(O[Si](C)(C)C(C)(C)C)C=C3O)C(=O)C3=C(O[Si](C)(C)C(C)(C)C)C=C(C)C=C3C5=C4C2=C1	5700.5	Semi standard non polar	33892256
Protohypericin,2TBDMS,isomer #6	CC1=CC(O)=C2C(=O)C3=C4C(=C(O)C=C3O[Si](C)(C)C(C)(C)C)C3=C5C(=C(O[Si](C)(C)C(C)(C)C)C=C3O)C(=O)C3=C(O)C=C(C)C=C3C5=C4C2=C1	5717.3	Semi standard non polar	33892256
Protohypericin,2TBDMS,isomer #7	CC1=CC(O)=C2C(=O)C3=C4C(=C(O)C=C3O[Si](C)(C)C(C)(C)C)C3=C5C(=C(O)C=C3O[Si](C)(C)C(C)(C)C)C(=O)C3=C(O)C=C(C)C=C3C5=C4C2=C1	5720.8	Semi standard non polar	33892256
Protohypericin,2TBDMS,isomer #8	CC1=CC(O)=C2C(=O)C3=C4C(=C(O)C=C3O)C3=C5C(=C(O[Si](C)(C)C(C)(C)C)C=C3O[Si](C)(C)C(C)(C)C)C(=O)C3=C(O)C=C(C)C=C3C5=C4C2=C1	5710.4	Semi standard non polar	33892256
Protohypericin,2TBDMS,isomer #9	CC1=CC(O)=C2C(=O)C3=C4C(=C(O[Si](C)(C)C(C)(C)C)C=C3O)C3=C5C(=C(O)C=C3O[Si](C)(C)C(C)(C)C)C(=O)C3=C(O)C=C(C)C=C3C5=C4C2=C1	5737.8	Semi standard non polar	33892256
Protohypericin,3TBDMS,isomer #1	CC1=CC(O[Si](C)(C)C(C)(C)C)=C2C(=O)C3=C4C(=C(O)C=C3O)C3=C5C(=C(O[Si](C)(C)C(C)(C)C)C=C3O)C(=O)C3=C(O[Si](C)(C)C(C)(C)C)C=C(C)C=C3C5=C4C2=C1	5742.0	Semi standard non polar	33892256
Protohypericin,3TBDMS,isomer #10	CC1=CC(O)=C2C(=O)C3=C4C(=C(O[Si](C)(C)C(C)(C)C)C=C3O)C3=C5C(=C(O[Si](C)(C)C(C)(C)C)C=C3O[Si](C)(C)C(C)(C)C)C(=O)C3=C(O)C=C(C)C=C3C5=C4C2=C1	5751.5	Semi standard non polar	33892256
Protohypericin,3TBDMS,isomer #2	CC1=CC(O[Si](C)(C)C(C)(C)C)=C2C(=O)C3=C4C(=C(O)C=C3O)C3=C5C(=C(O)C=C3O[Si](C)(C)C(C)(C)C)C(=O)C3=C(O[Si](C)(C)C(C)(C)C)C=C(C)C=C3C5=C4C2=C1	5741.0	Semi standard non polar	33892256
Protohypericin,3TBDMS,isomer #3	CC1=CC(O)=C2C(=O)C3=C4C(=C(O)C=C3O[Si](C)(C)C(C)(C)C)C3=C5C(=C(O[Si](C)(C)C(C)(C)C)C=C3O)C(=O)C3=C(O[Si](C)(C)C(C)(C)C)C=C(C)C=C3C5=C4C2=C1	5746.2	Semi standard non polar	33892256
Protohypericin,3TBDMS,isomer #4	CC1=CC(O)=C2C(=O)C3=C4C(=C(O)C=C3O[Si](C)(C)C(C)(C)C)C3=C5C(=C(O)C=C3O[Si](C)(C)C(C)(C)C)C(=O)C3=C(O[Si](C)(C)C(C)(C)C)C=C(C)C=C3C5=C4C2=C1	5747.2	Semi standard non polar	33892256
Protohypericin,3TBDMS,isomer #5	CC1=CC(O[Si](C)(C)C(C)(C)C)=C2C(=O)C3=C4C(=C(O)C=C3O)C3=C5C(=C(O[Si](C)(C)C(C)(C)C)C=C3O[Si](C)(C)C(C)(C)C)C(=O)C3=C(O)C=C(C)C=C3C5=C4C2=C1	5739.5	Semi standard non polar	33892256
Protohypericin,3TBDMS,isomer #6	CC1=CC(O[Si](C)(C)C(C)(C)C)=C2C(=O)C3=C4C(=C(O)C=C3O[Si](C)(C)C(C)(C)C)C3=C5C(=C(O)C=C3O[Si](C)(C)C(C)(C)C)C(=O)C3=C(O)C=C(C)C=C3C5=C4C2=C1	5750.5	Semi standard non polar	33892256
Protohypericin,3TBDMS,isomer #7	CC1=CC(O)=C2C(=O)C3=C4C(=C(O[Si](C)(C)C(C)(C)C)C=C3O)C3=C5C(=C(O)C=C3O[Si](C)(C)C(C)(C)C)C(=O)C3=C(O[Si](C)(C)C(C)(C)C)C=C(C)C=C3C5=C4C2=C1	5753.2	Semi standard non polar	33892256
Protohypericin,3TBDMS,isomer #8	CC1=CC(O)=C2C(=O)C3=C4C(=C(O)C=C3O)C3=C5C(=C(O[Si](C)(C)C(C)(C)C)C=C3O[Si](C)(C)C(C)(C)C)C(=O)C3=C(O[Si](C)(C)C(C)(C)C)C=C(C)C=C3C5=C4C2=C1	5745.0	Semi standard non polar	33892256
Protohypericin,3TBDMS,isomer #9	CC1=CC(O)=C2C(=O)C3=C4C(=C(O)C=C3O[Si](C)(C)C(C)(C)C)C3=C5C(=C(O[Si](C)(C)C(C)(C)C)C=C3O[Si](C)(C)C(C)(C)C)C(=O)C3=C(O)C=C(C)C=C3C5=C4C2=C1	5744.6	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Protohypericin GC-MS (Non-derivatized) - 70eV, Positive	splash10-056r-0100930000-12336cd4cee0283cdc28	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Protohypericin GC-MS (2 TMS) - 70eV, Positive	splash10-0079-5100059000-a013c10cef25f6b4ee31	2017-10-06	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Protohypericin 10V, Positive-QTOF	splash10-0a4i-0000290000-b285ed6a5bbc67d2561e	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Protohypericin 20V, Positive-QTOF	splash10-0a4i-0000590000-b687985249b486ac4934	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Protohypericin 40V, Positive-QTOF	splash10-0079-1000900000-59633c5f097a37bebecb	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Protohypericin 10V, Negative-QTOF	splash10-0a4i-0000090000-c055ae27121e2e0cd65a	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Protohypericin 20V, Negative-QTOF	splash10-0a4i-0000190000-70652925180413f71f54	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Protohypericin 40V, Negative-QTOF	splash10-000i-2000910000-c6565155993cc2f93715	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Protohypericin 10V, Negative-QTOF	splash10-0a4i-0000090000-6ebfacadbc229ed0c1c6	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Protohypericin 20V, Negative-QTOF	splash10-0a4i-0000090000-6ebfacadbc229ed0c1c6	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Protohypericin 40V, Negative-QTOF	splash10-0a4i-0000290000-e1e9d557e94689a83a64	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Protohypericin 10V, Positive-QTOF	splash10-0a4i-0000090000-cd3514b49df87a50d72d	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Protohypericin 20V, Positive-QTOF	splash10-0a4i-0000090000-cd3514b49df87a50d72d	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Protohypericin 40V, Positive-QTOF	splash10-004r-0000900000-7ddadd933a23e5889a23	2021-09-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB012472

KNApSAcK ID

C00034650

Chemspider ID

4590166

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5489488

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1699181

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for Protohypericin (HMDB0034180)

MOL for HMDB0034180 (Protohypericin)

3D MOL for HMDB0034180 (Protohypericin)

3D SDF for HMDB0034180 (Protohypericin)

3D-SDF for HMDB0034180 (Protohypericin)

PDB for HMDB0034180 (Protohypericin)

3D PDB for HMDB0034180 (Protohypericin)

SMILES for HMDB0034180 (Protohypericin)

INCHI for HMDB0034180 (Protohypericin)

Structure for HMDB0034180 (Protohypericin)

3D Structure for HMDB0034180 (Protohypericin)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra